WO2003014190A1 - Procede de production de mousses souples de polyurethanne - Google Patents

Procede de production de mousses souples de polyurethanne Download PDF

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Publication number
WO2003014190A1
WO2003014190A1 PCT/EP2002/007887 EP0207887W WO03014190A1 WO 2003014190 A1 WO2003014190 A1 WO 2003014190A1 EP 0207887 W EP0207887 W EP 0207887W WO 03014190 A1 WO03014190 A1 WO 03014190A1
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WO
WIPO (PCT)
Prior art keywords
ppm
compounds
flexible polyurethane
polyurethane foams
catalysts
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Ceased
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PCT/EP2002/007887
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German (de)
English (en)
Inventor
Stephan Bauer
Kathrin Harre
Raimund Ruppel
Edward Bohres
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BASF SE
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BASF SE
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Publication date
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Priority to EP02767218A priority Critical patent/EP1423454A1/fr
Priority to US10/484,600 priority patent/US20040192801A1/en
Publication of WO2003014190A1 publication Critical patent/WO2003014190A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
    • C08G65/2645—Metals or compounds thereof, e.g. salts
    • C08G65/2663—Metal cyanide catalysts, i.e. DMC's
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4866—Polyethers having a low unsaturation value
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/24—Nitrogen compounds
    • B01J27/26—Cyanides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0008—Foam properties flexible
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0041—Foam properties having specified density
    • C08G2110/005—< 50kg/m3
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0083—Foam properties prepared using water as the sole blowing agent

Definitions

  • the invention relates to a method for producing flexible polyurethane foams by reacting polyisocyanates with polyether alcohols.
  • polyurethanes has been known for a long time and has been described many times. It is usually carried out by reacting polyisocyanates with compounds having at least two hydrogen atoms reactive with isocyanate groups.
  • Polyols in particular polyether alcohols and / or polyester alcohols, are mostly used as compounds with two hydrogen atoms reactive with isocyanate groups.
  • the polyether alcohols are usually produced by catalytic addition of lower alkylene oxides, mostly ethylene oxide and / or propylene oxide, onto H-functional starter substances. Potassium hydroxide solution is mostly used as a catalyst in the technical production of polyether alcohols.
  • high molecular weight polyether alcohols such as are required especially when used for flexible polyurethane foams, side reactions occur with the use of potassium hydroxide as a catalyst, which lead to the formation of the so-called unsaturated constituents in the polyether alcohol.
  • These unsaturated components in the polyether alcohol are undesirable because they reduce the functionality of the polyether alcohols and also lead to odor problems in the polyether alcohols.
  • EP 759 450 (US Pat. No. 5,811,829) describes polyether alcohols produced by means of DMC catalysts and prepolymers prepared therefrom with a content of double metal cyanides in the range between 10 and 1000 ppm. These compounds should have better storage stability than those without this multimetal cyanide content. The use of these polyether alcohols and prepolymers for the production of flexible polyurethane foams is not described.
  • the core discoloration is observed especially at low densities of less than 40 kg / m3 and in particular of 30 kg / m3 due to the increasing temperature in the production of flexible polyurethane foams, in particular block flexible foams. In the worst case, the soft foams can burn off.
  • Non-ferrous metals include cadmium, cobalt, copper, nickel, lead, tin and zinc. These metals and their soluble compounds are mostly highly toxic to the human organism.
  • the object of the invention was to develop a process for the production of flexible polyurethane foams by reacting polyisocyanates with polyether alcohols which were produced by means of multimetal cyanide catalysts, in which no core discoloration occurs and which leads to foams and from which no heavy metal ions emerge can.
  • Production of flexible polyurethane foams can be used without core discolouration or other decomposition reactions if these contain a content of multimetal cyanide compounds in the range between 0.1 to 1000 ppm, in particular 1 to 500 ppm, preferably 10 to 200 ppm on
  • this corresponds to a cobalt content of 0.008 ppm to 80 ppm, preferably 0.8 ppm to 40 ppm and in particular 1.6 to 20 16 ppm and a zinc content of 0.02 ppm to 200 ppm, preferably 2 ppm to 100 ppm and in particular from 4 to 40 ppm, based on the standard polyether polyurethane flexible foam with a density of approx. 30 kg / m3.
  • the invention relates to a method for producing flexible polyurethane foams by reacting
  • a polyether alcohol which can be prepared by reacting alkylene oxides with H-functional starter substances in the presence of DMC catalysts and containing DMC catalysts in the range between 0 , 1 to 1000 ppm, based on the weight of the polyether alcohol, are used.
  • the invention further relates to flexible polyurethane foams without core discoloration, which can be produced by the process according to the invention.
  • the invention further relates to flexible polyurethane foams which have extractable heavy metals below the limits of the Oeko-Tex Standard 100 according to product classes 2 to 4 of:
  • the extraction is carried out with a foam body with the dimensions 100 x 100 x 50 mm using artificial sweat according to DIN 53160-2.
  • the welding simulant has a pH of 6.5 ⁇ 0.1.
  • composition of the sweat simulant is as follows:
  • Lactic acid (> 88% by mass) 1.0 g / 1
  • the foam body is stored in approx. 500 ml of artificial sweat in a migration cell with a cover for 24 hours at 40 ° C. After storage, the foam body is separated from the migration solution, the migration solution in the foam being removed by dripping.
  • the quantitative detection is determined using an atomic desoption spectrometer or inductively coupled plasma (ICP).
  • the invention further relates to the use of the flexible polyurethane foams produced by the process according to the invention for the manufacture of mattresses and furniture.
  • the multimetal cyanide compounds have no negative influence on the urethane formation reaction.
  • polyether alcohols used for the process according to the invention with a content of multimetal cyanide compounds in the range from 0.1 to 1000 ppm are, as described above, prepared by catalytic addition of alkylene oxides onto H-functional starter substances, using multimetal cyanide compounds as catalysts.
  • the multimetal cyanide compounds used to prepare the polyether alcohols used according to the invention are known. They mostly have the general formula (I)
  • M 1 is a metal ion selected from the group containing Zn2 +, Fe2 +, Co3 +, Ni2 +, Mn2 +, Co2 +, Sn2 +, Pb2 +, Mo4 +, Mo6 +, A13 +, V4 +, V5 +, Sr2 +, W4 +, W6 +, Cr2 +, Cr3 +, Cd2 +, Hg2 + , Pd2 +, Pt2 +, V2 +, Mg2 +, Ca2 +, Ba2 +, Cu2 +,
  • M 2 is a metal ion selected from the group containing Fe2 +, Fe3 +, Co2 +, Co3 +, Mn2 +, Mn3 +, V4 +, V5 +, Cr2 +, Cr3 +, Rh3 +, Ru2 +, Ir3 +
  • A is an anion selected from the group consisting of halide, hydroxide, sulfate, carbonate, cyanide, thiocyanate, isocyanate, cyanate, carboxylate, oxalate or nitrate,
  • X is an anion selected from the group consisting of halide, hydroxide, sulfate, carbonate, cyanide, thiocyanate, isocyanate, cyanate, carboxylate, oxalate or nitrate,
  • L is a water-miscible ligand selected from the group comprising alcohols aldehydes, ketones, ethers, polyether esters, ureas, amides, nitriles, lactones, lactams and sulfides,
  • e represents the coordination number of the ligand or 0
  • f represents a fractional or whole number greater than or equal to 0
  • h represents a fractional or whole number greater than or equal to 0.
  • These compounds are prepared by generally known processes, by combining the aqueous solution of a water-soluble metal salt with the aqueous solution of a hexacyanometallate compound, in particular a salt or an acid, also referred to below as educt solutions, and, if appropriate, during or after the combination gives a water soluble ligand.
  • a hexacyanometallate compound in particular a salt or an acid, also referred to below as educt solutions
  • Such catalysts and their preparation are described for example in EP 862,947 and DE 197,42,978.
  • Multimetal cyanide compounds are particularly advantageous for use as catalysts, and the corresponding acids are used in their preparation as cyanometallate compounds.
  • the multimetal cyanide compounds preferably have a crystalline structure. Their particle size is preferably in the range between 0.1 and 100 ⁇ m.
  • a particular advantage of the crystalline DMC catalysts, in particular those which have been prepared using cyanometalic acids, is their higher catalytic activity.
  • the polyether alcohols can be prepared using a smaller amount of catalyst. The amount used in this case mostly corresponds to the amount of multimetal cyanide compounds according to the invention in the finished polyether alcohol. The elaborate removal of the multimetal cyanide compounds from the polyether alcohol after production can thus be dispensed with.
  • multimetal cyanide compounds are preferably used in the form of suspensions, the multimetal cyanide compounds being suspended in organic compounds, preferably alcohols.
  • polyether alcohols used for the process according to the invention are produced, as stated, by adding alkylene oxides to H-functional starter substances using the catalysts described.
  • alkylene oxides can be used as alkylene oxides, for example ethylene oxide, propylene oxide, butylene oxide, styrene oxide, in particular ethylene oxide, propylene oxide and mixtures of the compounds mentioned are used as alkylene oxides.
  • H-functional compounds are used as starting substances.
  • alcohols with a functionality of 1 to 8, preferably 2 to 8, are used.
  • the starting substances used are, in particular, alcohols with a functionality of 2 to 4, in particular 2 and 3.
  • examples are ethylene glycol, propylene glycol, glycerin, trimethylolpropane, pentaerythritol.
  • alkylene oxides are added by means of DMC catalysts, it is advantageous to use their reaction products with alkylene oxides, in particular propylene oxide, together with or instead of the alcohols mentioned.
  • Such compounds preferably have a molecular weight of up to 500 g / mol.
  • the addition of the alkylene oxides in the production of these reaction products can take place with any catalysts, for example with basic catalysts.
  • the polyether alcohols for the production of flexible polyurethane foams mostly have a hydroxyl number in the range between 20 and 100 mgKOH / g.
  • the addition of the alkylene oxides in the production of the polyether alcohols used for the process according to the invention can be carried out by the known processes. It is possible that the polyether alcohols contain only one alkylene oxide. When using several alkylene oxides, a so-called blockwise addition, in which the alkylene oxides are added one after the other, or a so-called statistical addition, in which the alkylene oxides are metered in together, is possible. It is also possible to incorporate both block-by-block and statistical sections into the polyether chain in the production of the polyether alcohols.
  • Polyether alcohols having a high content of secondary hydroxyl groups and a content of ethylene oxide units in the polyether chain of at most 30% by weight, based on the weight of the polyether alcohol are preferably used for the production of flexible polyurethane foams.
  • These polyether alcohols preferably have a propylene oxide block at the chain end.
  • polyether alcohols with a high content of primary hydroxyl groups and an ethylene oxide end block in an amount of ⁇ 20% by weight, based on the weight of the polyether alcohol are used for the production of flexible molded polyurethane foams.
  • the alkylene oxides are preferably added under the conditions customary for this, at temperatures in the range from 60 to 180 ° C., preferably between 90 to 140 ° C., in particular between 100 to 130 ° C. and pressures in the range from 0 to 20 bar in the range from 0 to 10 bar and in particular in the range from 0 to 5 bar.
  • the mixture of starter substance and DMC catalyst can be pretreated by stripping before the start of the alkoxylation according to the teaching of WO 98/52689.
  • the polyether alcohol is worked up by customary processes in that the unreacted alkylene oxides and volatile constituents are removed, usually by distillation, steam or gas stripping and or other methods of deodorization. If necessary, filtration can also be carried out.
  • the DMC catalyst content according to the invention in the polyether alcohol can, as stated, be adjusted in various ways. It is thus possible, before the start of the reaction, to use the amount of DMC catalyst which corresponds to the content of this compound in the end product according to the invention. If a higher amount of DMC catalyst is used in the production of the polyether alcohols, the excess fraction can be removed from the polyether alcohol after the reaction.
  • the usual and known methods of cleaning the polyether alcohols are suitable for this, for example the filtration, which can be carried out as a deep filtration or by means of a membrane, or sedimentation, for example by means of centrifugation.
  • the polyether alcohols thus produced are, as described, preferably used as starting materials for the process according to the invention for the production of flexible polyurethane foams.
  • isocyanates with two or more isocyanate groups in the molecule are used as polyisocyanates.
  • Both aliphatic isocyanates such as hexamethylene diisocyanate (HDI) or isophorone diisocyanate (IPDI), or preferably aromatic isocyanates, such as tolylene diisocyanate (TDI), diphenylmethane diisocyanate (MDI) or mixtures of diphenylmethane diisocyanate and polymethylene polyphenylene polyisocyanates (crude) can be used.
  • TDI tolylene diisocyanate
  • MDI diphenylmethane diisocyanate
  • CAde polymethylene polyphenylene polyisocyanates
  • isocyanates which have been modified by the incorporation of urethane, uretdione, isocyanurate, allophanate, uretonimine and other groups, so-called modified isocyanates.
  • TDI is used in particular for the production of flexible flexible foams
  • MDI and its higher homologues are preferably used in the production of molded foams.
  • Polyols can preferably be used as compounds having at least two groups which are reactive with isocyanate groups and are used in a mixture with the polyether alcohols according to the invention.
  • the polyether polyols and the polyester polyols are of the greatest technical importance.
  • the polyether polyols used for the production of polyurethanes are mostly produced by base-catalyzed addition of alkylene oxides, in particular ethylene oxide and / or propylene oxide, onto H-functional starter substances.
  • Polyester polyols are usually made by esterifying polyfunctional carboxylic acids with polyfunctional alcohols.
  • the compounds with at least two groups reactive with isocyanate groups also include the chain extenders and / or crosslinking agents, which can optionally also be used. These are at least two-functional amines and / or alcohols with molecular weights in the range from 60 to 400.
  • the blowing agents used are mostly water, at the reaction temperature of the urethane reaction gaseous compounds which are inert to the starting materials of the polyurethanes, so-called physically active blowing agents, and mixtures thereof.
  • the most common physical blowing agents are hydro- Substances with 2 to 6 carbon atoms, halogenated hydrocarbons with 2 to 6 carbon atoms, ketones, acetals, ethers, inert gases such as carbon dioxide or noble gases are used.
  • a catalysts and / or metal compounds, in particular heavy metal salts and / or organometallic compounds, are preferably used as catalysts.
  • known tertiary amines and / or with organic metal compounds are used as catalysts.
  • organic metal compounds e.g. Tin compounds in question, such as
  • Tin (II) salts of organic carboxylic acids e.g. Tin (II) acetate, tin (I ⁇ ) octoate, tin (II) ethylhexoate and tin (II) laurate and the dialkyltin (IV) salts of organic carboxylic acids, e.g. Dibutyltin diacetate, dibutyltin dilaurate, dibutyltin maleate and dioctyltin diacetate.
  • organic amines which are customary for this purpose are: triethylamine, 1,4-diazabicyclo [2,2,2] octane, tributylamine, dimethylbenzylamine, N, N, N ', N'-tetramethylethylenediamine, N , N, N ', N' -tetramethyl-butanediamine, N, N, N ', N' -tetramethyl-hexane-1,6-diamine, dimethylcyclohexylamm.
  • the catalysts described can be used individually or in the form of mixtures.
  • organic metal compounds as catalysts, since these are best compatible with the multimetal cyanide compounds.
  • Release agents, flame retardants, dyes, fillers and / or reinforcing agents are used as auxiliaries and / or additives.
  • the polyurethanes can be produced by the so-called one-shot process or by the prepolymer process.
  • the flexible polyurethane foams can be block foams as well as molded foams.
  • the soft foams produced in the amount according to the invention in the presence of multimetal cyanide compounds in the polyether alcohols show a significantly improved curing behavior without crack formation compared to those which had a lower or higher content of multimetal cyanide compounds.
  • the flexible polyurethane foams produced by the process according to the invention show no or only an extremely low exposure to heavy metals even when exposed to moisture.
  • the metals are effectively fixed in the foam matrix.
  • the polyether alcohols according to the invention can be processed to flexible polyurethane foams with a high open cell or high air permeability and a trouble-free foam structure without crack formation and core combustion.
  • Example 2 Determination of the migration of cobalt from the foam material, according to Example 1
  • Simulants / test migration agents Artificial sweat according to DIN 53160 Migration conditions: 24 h at 40 ° C; the two test specimens - are each stored in approx. 500 ml artificial sweat in a migration cell with a cover -. Determination method: After storage and cooling to room temperature, the test specimen and migration solution were separated, the migration solution in the foam body being removed by dripping. Cobalt was determined by atomic spectroscopy in the Migrat.
  • the initial weight of the initial weight of the test specimens can be the maximum amount of extractable cobalt (Co) M ig rat i on, derived.
  • the value is w (Co) M i gra ti on . ⁇ 0.3 ⁇ g / kg.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Toxicology (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne un procédé de production de mousses souples de polyuréthanne consistant à faire réagir des a) polyisocyanates avec b) des composés comportant au moins deux atomes d'hydrogène réagissant avec des groupes isocyanates, en présence c) d'agents moussants. L'invention est caractérisée en ce qu'au moins un polyéther alcool pouvant être produit par réaction d'oxydes d'alkylène avec des substances de départ à fonction H en présence de catalyseurs DMC présents selon une quantité comprise entre 0,1 et 1000 ppm par rapport au poids du polyéther alcool, peut être utilisé comme composés (b) comportant au moins deux atomes d'hydrogène réagissant avec des groupes isocyanates.
PCT/EP2002/007887 2001-08-03 2002-07-16 Procede de production de mousses souples de polyurethanne Ceased WO2003014190A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP02767218A EP1423454A1 (fr) 2001-08-03 2002-07-16 Procede de production de mousses souples de polyurethanne
US10/484,600 US20040192801A1 (en) 2001-08-03 2002-07-16 Method for the production of polyurethane soft foam materials

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10137628A DE10137628A1 (de) 2001-08-03 2001-08-03 Verfahren zur Herstellung von Polyurethan-Weichschaumstoffen
DE10137628.6 2001-08-03

Publications (1)

Publication Number Publication Date
WO2003014190A1 true WO2003014190A1 (fr) 2003-02-20

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PCT/EP2002/007887 Ceased WO2003014190A1 (fr) 2001-08-03 2002-07-16 Procede de production de mousses souples de polyurethanne

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US (1) US20040192801A1 (fr)
EP (1) EP1423454A1 (fr)
DE (1) DE10137628A1 (fr)
WO (1) WO2003014190A1 (fr)

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WO2005121214A1 (fr) * 2004-06-09 2005-12-22 Shell Internationale Research Maatschappij B.V. Procede d'obtention d'un polyol de polyether a faible odeur
CN1329428C (zh) * 2004-12-07 2007-08-01 上海工程技术大学 一种除去聚醚多元醇中微量c1－c7低碳组分的方法

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CN100591644C (zh) * 2005-12-23 2010-02-24 中国科学院金属研究所 一种高导热、高强高密的SiC/Cu复相泡沫材料及其制备方法
CN100400473C (zh) * 2005-12-23 2008-07-09 中国科学院金属研究所 一种高强高韧SiC/Al泡沫材料及其制备方法
US10258953B2 (en) 2016-08-05 2019-04-16 Covestro Llc Systems and processes for producing polyether polyols

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WO2000074845A1 (fr) * 1999-06-02 2000-12-14 Basf Aktiengesellschaft Composes a base de cyanure polymetallique, leur procede de production et leur utilisation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005121214A1 (fr) * 2004-06-09 2005-12-22 Shell Internationale Research Maatschappij B.V. Procede d'obtention d'un polyol de polyether a faible odeur
CN1329428C (zh) * 2004-12-07 2007-08-01 上海工程技术大学 一种除去聚醚多元醇中微量c1－c7低碳组分的方法

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DE10137628A1 (de) 2003-02-27
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